7-(2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl)-4-[(2-methylpropanoyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate | 227950-66-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 7-(2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl)-4-[(2-methylpropanoyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate
• 英文别名: [7-[(2R,4S,5R)-5-[[bis(4-methoxyphenyl)-phenylmethoxy]methyl]-4-hydroxyoxolan-2-yl]-4-(2-methylpropanoylamino)pyrrolo[2,3-d]pyrimidin-2-yl] N,N-diphenylcarbamate
• CAS: 227950-66-5
• 化学式: C₄₉H₄₇N₅O₈
• 分子量: 833.941
• InChiKey: CALCDVZPVBHGHS-VDXPIPGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  62
• 可旋转键数：
  15
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  三乙基碳酸氢铵缓冲液 、 7-(2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl)-4-[(2-methylpropanoyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate 在 N-甲基吗啉 、 1H-1,2,4-三唑 、 三氯化磷 作用下， 以 二氯甲烷 为溶剂， 反应 0.58h， 以74%的产率得到7-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl]-4-[(2-methylpropanoyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate 3'-triethylammonium phosphonate
  参考文献：
  名称：

  The Base-Pairing Properties of 7-Deaza-2′-deoxyisoguanosine and 2′-Deoxyisoguanosine in Oligonucleotide Duplexes with Parallel and Antiparallel Chain Orientation

  摘要：

  Oligonucleotides with parallel (ps) or antiparallel (aps) chain orientation containing 7-deaza-2'-deoxyisoguanosine (1) or 2'-deoxyisoguanosine (2) were prepared. The phosphoramidite and phosphonate building blocks 3-6 were synthesized and used in solid-phase synthesis. The diphenylcarbamoyl (dpc) residue was used for the 2-oxo group protection and the isobutyryl (iBu = ib) residue fur the amino function. Hybridization experiments were performed with oligonucleotides containing 7-deazaisoguanine or isoguanine. Regarding 7-deazapurine-containing oligonucleotides, the 7-deazaisoguanine cytosine base pair was the strongest in ps-duplexes, while that of 7-deazaisoguanine.5-methylisocytosine was the most stable one in aps-DNA. Ambiguous base pairing of 7-deazaisoguanine with cytosine, 5-methylisocytosine, thymine, and guanine was observed in the case of aps-duplexes, whereas in ps-duplexes, the ambiguity was extended to adenine. The 7-deazaisoguanine-containing duplexes showed almost identical base-pair stabilities as those containing isoguanine. According to this, various base-pair motifs are proposed. The 7-deaza-2'-deoxyisoguanosine was found to be an effective substitute of 2'-deoxyisoguanosine.

  DOI：

  10.1002/(sici)1522-2675(19990505)82:5<726::aid-hlca726>3.0.co;2-k
• 作为产物：
  描述：

  4-amino-7-(2'-deoxy-β-D-erythro-pentofuranosyl)-3,7-dihydro-2H-pyrrolo<2,3-d>pyrimidin-2-one 在 吡啶 、 三甲基氯硅烷 、 N,N-二异丙基乙胺 作用下， 生成 7-(2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-erythro-pentofuranosyl)-4-[(2-methylpropanoyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-2-yl diphenylcarbamate
  参考文献：
  名称：

  7-Deazaisoguanine quartets: self-assembled oligonucleotides lacking the Hoogsteen motif

  摘要：

  含有连续 7-去氮异鸟嘌呤残基的寡核苷酸形成了自组装四元组，表明异鸟嘌呤的嘌呤氮-7 没有参与氢键模式。

  DOI：

  10.1039/a704866a

文献信息

• Oligonucleotides Containing Consecutive 2′-Deoxy-Isoguanosine Residues: Synthesis, Parallel Duplex Formation and Identification of a d(T₄iG₄T₄) Tetraplex
  作者：Frank Seela、Changfu Wei、Alexander Melenewski

  DOI：10.1080/07328319708006221

  日期：1997.7

  Oligonucleotides containing consecutive 2'-deoxyisoguanosines were synthesized by using building blocks protected with a diphenylcarb-amoyl residue. Parallel duplexes were formed by iG(d)-dC base pairs and a tetraplex of d(T(4)iG(4)T(4)) was identified by ion exchange HPLC.